In 1936, the 17 year-old Buccieri was arraigned in a Chicago court on charges of petty larceny. When judge said that he was going to send the charges to a grand jury, Buccieri's brother Fiore asked if the family could punish him instead. The judge agreed and one of Buccieri's relatives gave him five lashes with a doubled five-foot length of rubber hose. This would be Buccieri's only arrest in a lifetime of crime. During the 1960s, Buccieri was a business manager for illegal gambling and loansharking operations on Chicago's West Side.